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Leave the window in storage for a year and then install it over the weekend.

The same place that would rent the drop deck trailer probably also has a forklift. You can probably have one delivered in the morning, have use of it all day, and wave goodbye to it in the afternoon for under $500. It's not a bad price all things considered.

Forklift, skid steer, or tractor with loader would be easy. Failing that, rent a drop deck trailer and have the delivery driver set it on there. Strap it down and take it to where it needs to land. Failing that, removing the compressor head and motor eliminates the top heavy problem. Then...

How about a piece of solid corrugated drain pipe? Slit it to install and you can use zip ties to cinch it up.

Nothing says those 4x8 sheets of 5/8" fire rated drywall need to be installed seamlessly. It's roughly 2.2 lbs psf. Ripped in half along either axis and you're looking at about 35 lbs per piece, which is probably manageable. If the seams are cause for concern you could fire caulk them before...

What is your use case for the 16' tall garage bay? That's RV/semi storage height, but your door is to low for this use. It's just a waste of space for passenger vehicle use no matter what lift you choose. The smaller doors I would make 1' taller/wider if possible. I would not bother heating a...

You're considering installing new decking over deteriorated structure? "There is some rot in the screw holes but otherwise the framing looks good." Do you anticipate that rot will improve once you install the new decking?

If you can't drive through, you may have a lot that is conducive to driving under. How about building a full basement under the main shop?

Powered gable vent.

If you are expecting concrete to self-level you are going to be wildly disappointed.

Regarding your thoughts on the existing barn to be torn down/replaced: check with whomever has final authority over your plans to be sure if you tear that building down you are allowed to put another up in the same location. Frequently, when setbacks are changed after the fact, existing...

This may not work since that's a shared wall, but I have used an angle grinder with a diamond blade to grind a nice flat dado in a rough stone wall. Provided support for the stringer and eliminated all of the individual scribing.

If I wanted the attic space bad enough, converting a portion of the wall (or the entire thing) into a truss is probably the path I'd take. Could also replace part of the top of the wall with some LVLs and suspend what's beneath it or put the LVLs on the bottom and have everything above bear on...

Insulation alone won't do much. You need to fully control the climate. The temperature of the air can change much more rapidly than your much denser metal tools. When this happens, condensation forms on the surface which eventually turns into rust. You would need heat and AC in the shed to...

If you're going to raise the roof it would probably be faster to rebuild completely from scratch. Not necessarily cheaper, but faster, and you could make any other changes you want at the same time. Gutters will help with the bottom rot, but won't eliminate it. Water proofing/painting after...

Racedeck and sawdust sounds like a nightmare best avoided if possible. Polished concrete, epoxy, porcelain, etc. are all superior options for a space that that will house autos and woodwork, even if their cohabitation is infrequent. Most power companies are perfectly willing to relocate a pole...

Check with whomever needs to sign off on your installation. Some locations frown on shared trenches, some don't care as long as certain clearances are maintained. I would run them side by side rather than one on top of the other. Whichever needs service will always be on the bottom.

To confirm I understand correctly: the pictured living room (very nice) is on the first floor, there are two bedrooms directly above with a shared wall that runs roughly across the middle of the living room and the trussish structure is in the attic directly above the wall separating the...

You may want to consider an in ground scissor lift with that fixed width.

The dirt can be moved via most any means. The bigger challenge is controlling the water. Your dirtscaper would need to create a swale to catch and direct that water away from the structure. Extending the retaining wall out a sidewalk's width or so is another option.